Basic information
- Standard SMILES
COc1ccc(C(=O)O)cc1- InChIKey
ZEYHEAKUIGZSGI-UHFFFAOYSA-N- Molecular formula
- C8H8O3
- Average molar mass
- 152.15 g/mol
- Monoisotopic mass
- 152.04734412
Overview
4-methoxybenzoic acid is a methoxybenzoic acid substituted with a methoxy group at position C-4. It has a role as a plant metabolite. It is functionally related to a benzoic acid. It is a conjugate acid of a 4-methoxybenzoate.
Names & identifiers
- Preferred name
- 4-Methoxybenzoic Acid
- IUPAC
- 4-methoxybenzoic acid
- English name
- 4-Methoxybenzoic acid
- Molecular formula
- C8H8O3
- Molecular weight
- 152.15
Names & synonyms
4-METHOXYBENZOIC ACIDp-Anisic acid100-09-4p-Methoxybenzoic acidDraconic acidBenzoic acid, 4-methoxy-4-Anisic acidANISIC ACID, PARApara-anisic acid4SB6Y7DMM3NSC-32742DTXSID4059205
Show more names
p-Anisic acid (4-Methoxybenzoic acid)FEMA 3945Anisic4-Methoxybenzoic
FEMA NO. 3945CHEBI:40813RefChem:44617DTXCID0032445202-818-5ANISIC ACID1335-08-6MFCD00002542
Database identifiers
- CAS
100-09-4、1335-08-6- PubChem CID
- 7478
- DTXSID
DTXSID4059205- ChEMBL
CHEMBL21932- ChEBI
CHEBI:40813- UNII
- 4SB6Y7DMM3
- EC Number
- 202-818-5、215-618-8
- Nikkaji
- J3.229H
Properties
Computed structural properties
- XLogP
- 2
- Topological polar surface area
- 46.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 136
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Benzoic Acid Derivatives
DrugsPharmaceuticals -> Listed in ZINC15
CosmeticsMasking
SpringerMaterials PropertiesBoiling point
LogP1.96
Food Additives
FLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Solubility
0.53 mg/mL at 37 °C
soluble in boiling water, organic solvents
freely soluble (in ethanol)
Endocrine DisruptorsPotential endocrine disrupting compound
Boiling Point275-280 °C
Melting Point185 °C
Vapor Pressure0.0015 [mmHg]
Physicochemical properties
- Melting point
- 182 · 182-185 °C(lit.)
- Boiling point
- 275 °C · 275 °C
- Density
- 1.385 · 1.385
- bulk density
- 380 kg/m3 · 380kg/m3
- vapor pressure
- 0.001 Pa · 0.001Pa at 25℃
- FLAVIS Number
- 8.071 · 08.071 | p-Anisic acid
- refractive index
- 1.571 · 1.571-1.576
- FEMA
- 3945 · 3945 | 4-METHOXYBENZOIC ACID
- Flash point
- 185 °C · 185 °C
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- 2 O: · H2O: soluble2500 parts
- form
- Powder
- pka
- 4.5 · 4.50(at 25℃)
- color
- White to slightly gray-beige
- PH
- 3 · 3-4 (0.3g/l, H2O, 20℃)
- Odor
- 10 % · at 10.00 % in dipropylene glycol. faint putrid sweet cadaverous
- Odor Type
- animal
- biological source
- synthetic
- Water Solubility
- 20 °C · Soluble in water at 20°C 0.3g/L. Soluble in alcohol, ethyl acetate and ether.
- Merck
- 14 · 14,666
- JECFA Number
- 883 · 883
- BRN
- 508910 · 508910
- Henry's Law Constant
- 1.8 · 1.8×103 mol/(m3Pa) at 25℃, Abraham and Jr. (2019)
- Stability
- Stable. Incompatible with strong oxidizing agents.
- Major Application
- food and beveragespharmaceutical
- Cosmetics Ingredients Functions
- FRAGRANCE
- InChI
- 1S/C8H8O3/c1-11-7-4-2-6(3-5-7)8(9)10/h2-5H,1H3,(H,9,10)
- InChIKey
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N
- SMILES
- COc1ccc(cc1)C(O)=O
- LogP
- 1.96 · 1.96
- Substances Added to Food (formerly EAFUS)
- 4 · 4-METHOXYBENZOIC ACID
- CAS DataBase Reference
- 100 · 100-09-4(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 4 SB6Y7DMM3 · 4SB6Y7DMM3
- NIST Chemistry Reference
- 4 · Benzoic acid, 4-methoxy-(100-09-4)
- EPA Substance Registry System
- 4 · Benzoic acid, 4-methoxy- (100-09-4)
- UNSPSC Code
- 85151701 · 85151701
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 264 · P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P261-P305+P351+P338-P301+P312+P330
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi,Xn
- Risk Statements
- 36 · 36/37/38-22
- Safety Statements
- 26 · 26-36-24/25
- WGK Germany
- 1 · 1
- RTECS
- 4395000 · BZ4395000
- Autoignition Temperature
- 185 °C · 185 °C
- Hazard Note
- Irritant
- TSCA
- TSCA listed
- HS Code
- 29189090 · 29189090
- Storage Class
- 13 · 13 - Non Combustible Solids
- Toxicity
- 50 orally · LD50 orally in Rabbit: > 5000 mg/kg
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 57% (172 of 302) of all reports.
Warning
H302 (38.4%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 302 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Benzoic acid, 4-methoxy-
Chemical: Benzoic acid, methoxy-
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Status: Active Update: 28-01-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/24279
Benzoic acid, 4-methoxy-: Does not have an individual approval but may be used under an appropriate group standard
Other Safety Information
Evaluation - Chemicals not considered for in depth evaluation - Not commercially active in Australia
IMAP assessments - Benzoic acid, 4-methoxy-: Environment tier I assessment
Hazards SummarySafe when used as a flavoring agent in food; [JECFA] A skin and strong eye irritant; Harmful by ingestion; [Sigma-Aldrich MSDS]
Hazard Classes and CategoriesAcute Tox. 4 (38.4%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- BZ4395000
- hs_code
- 29189090
- Toxicity
- LD50 orally in Rabbit: > 5000 mg/kg
- risk_code
- 36/37/38-22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi,Xn
- hazard_note
- Irritant
- safety_code
- 26-36-24/25
- Storage Class
- 13 - Non Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- REACH Registrations
- Active
- Autoignition Temperature
- 185 °C
- Precautionary statements
- P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P261-P305+P351+P338-P301+P312+P330
Chemistry & industry
Uses & manufacturing
UsesUsed as flavoring agent or adjuvant; [FDA]
Household ProductsInformation on 14 consumer products that contain p-Anisic acid in the following categories is provided:
Use Classification
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing InformationBenzoic acid, 4-methoxy-: ACTIVE
Applications
DescriptionP-Anisic acid, also known as 4-Methoxybenzoic acid or draconic acid, is an organic acid that has a sweet flavor. It is one of the isomers of anisic acid, including m-anisic acid and o-anisic acid. The term "anisic acid" often refers to this form specifically. P-anisic acid is produced through the oxidation of p-cresyl-methyl ether.
Uses4-Methoxybenzoic acid (p-Anisic acid) is used in oxidation and reduction of cytochrome c in solution through different self-assembled monolayers on gold electrodes using cyclic voltammetry. p-Anisic acid has antiseptic properties. It is also used as an intermediate in the preparation of more complex organic compounds.
General Description4-Methoxybenzoic acid is the sole source of carbon and energy for growth in the cultures of Nocardia sp. DSM 1069. It is effective in clearing congestion in the lungs and the respiratory tracts in conditions like asthma or bronchitis.
Preparation methods
PreparationTo obtain 4-Methoxybenzoic acid, the mole ratio of cobalt and manganese is modified and p-methoxy toluene is reacted with oxygen or an oxygen-containing gas in the presence of acetic acid. The following is the experimental procedure:1. Using n-hexyl bromide, tri (n-hexyl) amine, para-methoxy toluene with cobalt chloride hexahydrate in about 9h;2. By a catalytic oxidation process using p-methoxy toluene and propionic acid over a catalyst comprising of CoBr2.6H2O and MnBr2.4H2O with a reaction time of 20h;3. Through changing the mole ratio of cobalt and manganese, using p-methoxy toluene with oxygen or oxygen containing gas in the presence of acetic acid to obtain the product.
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
DefinitionChEBI: 4-methoxybenzoic acid is a methoxybenzoic acid substituted with a methoxy group at position C-4. It has a role as a plant metabolite. It is functionally related to a benzoic acid. It is a conjugate acid of a 4-methoxybenzoate.
Related reactions
403 records
Linked notes
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